1. Field of the Invention
This invention relates to processes for preparing 1-alkylamino-3-(5-substitutedaminocarbonylthiazol-2-yloxy)-propan-2-ols and 3-(5-substitutedaminocarbonylthiazol-2-yloxy)-1,2-epoxypropanes; 5-(5-substitutedaminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazolidines and derivatives thereof. In a further aspect this invention relates to 2-alkylsulfinyl-5-substituted aminocarbonylthiazoles and 2-alkylsulfonyl-5-substitutedaminocarbonylthiazoles and to processes for preparing such compounds.
2. The Prior Art
The present invention relates to improved processes and intermediates for preparing certain 1-alkylamino-3-(5-substitutedaminocarbonylthiazol-2-yloxy)-propan-2-ol .beta.-blocking cardiovascular agents. These cardiovascular agents are typically prepared by a multistep process (note U.S. Pat. Nos. 3,896,139 and 3,897,441) requiring the conversion of the appropriate 2-halothiazole (or 5-substituted 2-halothiazole) to the corresponding thiazol-2-yloxy propanediol acetonide; thence to the diol; then to the mesylate and then finally to the corresponding 3-(5-substitutedaminocarbonylthiazol-2-yloxy)-1,2-epoxypropane which is then easily converted to the final product via treatment with the desired alkylamine. In contrast to this, the 1,2-epoxypropane intermediate is prepared in the present process, in a single step either directly from the corresponding 2-halothiazole or from the corresponding 2-sulfinyl or 2-sulfonylthiazole. The present invention also relates to improved processes for preparing certain 5-(thiazol-2-yloxymethylene)-N-alkyloxazolidines and derivatives thereof, which can be conducted at lower temperatures and afford purer products than the prior art processes described in the aforementioned U.S. patents.